Thiazyl sulphur halide



Patented Oct. 7, 1941 '1. 2 257 974 wUNtit- ;-j -STAit PATENT;

William E. Messer, Cheshire, Conn., assignor to United States Rubber Company, New York, v N. Y., a corporationoi New Jersey No Drawing. Application June 22, 1939, I jSerialNo. 280,446

8 Claims. (01. 260-306)" This inventionrelates to a new class of coming range is 132-135 C. and decomposes at about pounds. o I v j I r i this point.

The new products are compounds comprising Analysis the-group? v Y I '7 I I i Found Calculated VI 1.; OXhalogen- I I f Y ,Pe'rcent .Percmt N1trogenL 6. 6.9 ulphur 31-.2 131,8 v a preferred member being benzothiaeyl Sulphur Instead of the benz othiazole'disulphidefthere f X represents Sulphur: selemum may be used the corresponding disulphides of the lurium. naphthalene and anthracene series.

They may be P p by pawng or mcorpo By using bromine, or iodine, the correspondrating the halogen nto a suspension or slurry of mg thiazyl Sulphur bromide, and iodides may be a compound containing the group prepared. Benzothiazyl sulphur bromide is an orange, reddish colored fuming powder, M. P. 80-100 0., with decomposition. Benzothiazyl sulphur iodide is a brown powder, M. P. 105-125 ll C., with decomposition.

--N NG Examples of other thiazyl sulphur halides within the scope of the invention are:

in an organic solvent such as benzene. tetrachlor H ethylene, carbon tetrachloride, etc., which is unreactive with the halogen, until substantially ll complete solution ensues and at least the theoretical amount of halogen has been absorbed; After heating to remove excess halogen, he ho solution is freed of insoluble matter that may be filmy] Sulphur chlonde formed and cooled.. By evaporating oflf the solvent or cooling the clear solution the present products may be recovered as residues or precipitates. N

The following example illustrates the invenehlor-benzothiazyl sulphur chloride tion, in which benzothiazyl sulphur chloride s C-S-Cl CSchlorine \N/ 40 is prepared:

Example naphthothiazyl sulphur chloride 33 grams (1 mole) 1,l'-dithio bis benzo thiazole and the corresponding bromides, and iodides. (di-(benzothiazyl) -disulphide) are shaken with The compounds may be used as intermediates, 200 005. drycarbon tetrachloride and dry chlorine in the preparation of various derivatives of merpassed in over liquid for 20 minutes with occacapto-aryl-thiazoles in which the halogen is resional shaking until all was dissolved. Heated placed with suitable radicals, in the production to 70:C. to drive off excess chlorine. Clear of vulcanization accelerators. Other uses are light reddish liquid is decanted from trace of tar also contemplated. When used as intermediates, and evaporated on water bath leaving 39+ grams they are best used freshly prepared and in soof benzothiazyl sulphur chloride (theory=40 lution.

grams). It is a yellowish crystalline powder Having thus described my invention, what I which tends to fume rapidly in moist air. Meltclaim and desire to protect by Letters Patent is;

1. As new products, compounds having the general formula /.\s/ where AR. represents an arylene group; where X is an element or the group consisting of divalen sulphur, selenium, and tellurium. I

2. As new compounds, arylenethiazyl halides of the general formula A R S ha l ogen where AR represents an arylene group. 5 14 sulphur 7 phur halides which comprises reacting a suspensiOn of a di(arylenethiazyl) -disulphide in an organic solvent inert to substantially dry halogen, with substantially dry halogen, until substantially complete solution of the suspension occurs.

6. A process of preparing arylenethiazyl sulphur chlorides which comprises reacting a suspension of a di(arylene-thiazyl) disulphide in an organic solvent inert to substantially dry chlorine, with substantially dry chlorine, until substantially complete solution of the suspension "occurs. I 7.;A- process of preparing thiazyl sulphur halides which comprises reacting a suspension of a di(thiazyl) +disulphide in an organic solvent inert to substantially dry halogen, with substantially 3. As new products, compounds having the general formula W. ,C-X-halogen V a s where Xis an*e1ement of the group' consisting'o'f divalent sulphur, selenium, and tellurium.

4. As a new compound, benzothiazyljsulphur chloride, M.

5. A process.of "aasuigayiaaaaa si ii I dry halogen, until substantially complete solution of the suspension occurs, and separating the WILLIAM E. MESSER; 

